Controlling thread assemblies of pharmaceutical compounds in liquid crystal phase by using functionalized nanotopography

Chemistry of Materials

Volumn 22, Issue 8, 2010, Pages 2434-2441

  Simon, Karen A ^a   Burton, Erik A ^a   Cheng, Fei ^a   Varghese, Nisha ^a   Falcone, Eric R ^a   Wu, Lei ^a   Luk, Yan Yeung ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CHAINS; ALKANETHIOLS; AZIMUTHAL DIRECTION; CHROMONIC LIQUID CRYSTALS; DRUG MOLECULES; DYE MOLECULE; FUNCTIONALIZED; GLASS SLIDES; GOLD DEPOSITION; GOLD FILM; HYDRATED MOLECULES; INCIDENT ANGLES; LARGE SURFACE AREA; LIQUID CRYSTAL PHASE; LIQUID CRYSTAL PHASIS; LONG DISTANCES; MOLECULAR ARRANGEMENTS; MOLECULAR ASSEMBLY; NANOTOPOGRAPHIES; NON-TOXICITY; ODD-EVEN EFFECTS; OPTICAL CELLS; PHARMACEUTICAL COMPOUNDS; SAMS; SUNSET YELLOWS; SURFACE APPROACH; SURFACE NORMALS;

BIOCHEMISTRY; ETHYLENE; ETHYLENE GLYCOL; FUNCTIONAL GROUPS; GLASS; GOLD; GOLD DEPOSITS; HYDRATES; HYDRATION; HYDRAULIC STRUCTURES; LIQUID CRYSTALS; METALLIC FILMS; MOLECULES; SELF ASSEMBLED MONOLAYERS;

GOLD COATINGS;

EID: 77951243913     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm901477a     Document Type: Article

References (104)

1. Kato, T.; Okamoto, I.; Masu, H.; Katagiri, K.; Tominaga, M.; Yamaguchi, K.; Kagechika, H.; Azumaya, I. Cryst. Growth Des. 2008, 8 (10) 3871-3877
2. Thun, J.; Seyfarth, L.; Senker, J.; Dinnebier, R. E.; Breu, J. Angew. Chem., Int. Ed. 2007, 46 (35) 6729-6731
3. Miller, J. S. CrystEngComm 2005, 7, 458-461
4. Desiraju, G. R. Cryst. Growth Des. 2004, 4 (6) 1089-1090
5. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. 2004, 7, 890-891
6. Hollingsworth, J. A.; Poojary, D. M.; Clearfield, A.; Buhro, W. E. J. Am. Chem. Soc. 2000, 122 (14) 3562-3563
7. Holman, K. T.; Pivovar, A. M.; Ward, M. D. Science 2001, 294 (5548) 1907-11
8. Bataille, T.; Costantino, F.; Ienco, A.; Guerri, A.; Marmottini, F.; Midollini, S. Chem. Commun. 2008, 47, 6381-6383
9. Mondal, R.; Howard, J. A. K. CrystEngComm 2005, 7, 462-464
10. Seddon, K. R. Cryst. Growth Des. 2004, 4 (6) 1087
11. Prabakaran, P.; Umadevi, B.; Panneerselvam, P.; Muthiah, P. T.; Bocelli, G.; Righi, L. CrystEngComm 2003, 5, 487-489
12. Nangia, A.; Desiraju, G. R. Chem. Commun. 1999, 7, 605-606
13. Gorbitz, C. H.; Hersleth, H.-P. Acta Crystallogr., Sect. B: Struct. Sci. 2000, B56 (3) 526-534
14. Stevenson, C. L.; Bennett, D. B.; Lechuga-Ballesteros, D. J. Pharm. Sci. 2005, 94 (9) 1861-1880
15. Wunderlich, B. Thermochim. Acta 1999, 340-341, 37-52
16. Garcia-Garibay, M. A. Proc. Natl. Acad. Sci. U.S.A. 2005, 102 (31) 10771-10776
17. Desgranges, C.; Delhommelle, J. J. Am. Chem. Soc. 2006, 128 (47) 15104-15105
18. Lee, S.; Hoff, C. Large-scale aspects of salt formation: processing of intermediates and final products. In Handbook of Pharmaceutical Salts; Wiley-VCH: New York, 2008; pp 191 - 220.
19. Moribe, K.; Tozuka, Y.; Yamamoto, K. Adv. Drug Delivery Rev. 2008, 60 (3) 328-338
20. Veesler, S.; Puel, F.; Fevotte, G. STP Pharma Prat. 2005, 15 (1) 53-84
21. Bonafede, S. J.; Ward, M. D. J. Am. Chem. Soc. 1995, 117 (30) 7853-61
22. Sugawara, Y.; Nakamura, A.; Iimura, Y.; Kobayashi, K.; Urabe, H. J. Phys. Chem. B 2002, 106 (40) 10363-10368
23. Luk, Y.-Y.; Abbott, N. L. Curr. Opin. Colloid Interface Sci. 2002, 7 (5,6) 267-275
24. Han, Y.; Cheng, K.; Simon, K. A.; Lan, Y.; Sejwal, P.; Luk, Y.-Y. J. Am. Chem. Soc. 2006, 128 (42) 13913-13920
25. Chow, K.; Tong, H. H. Y.; Lum, S.; Chow, A. H. L. J. Pharm. Sci. 2008, 97 (8) 2855-2877
26. 3OH on obliquely deposited gold films.
27. Skaife, J. J.; Abbott, N. L. Chem. Mater. 1999, 11 (3) 612-623
28. Nakata, M.; Zanchetta, G.; Chapman, B. D.; Jones, C. D.; Cross, J. O.; Pindak, R.; Bellini, T.; Clark, N. A. Science 2007, 318 (5854) 1276-1279
29. Link, D. R.; Natale, G.; Shao, R.; Maclennan, J. E.; Clark, N. A.; Korblova, E.; Walba, D. M. Science 1997, 278 (5345) 1924-1927
30. Klaikherd, A.; Nagamani, C.; Thayumanavan, S. J. Am. Chem. Soc. 2009, 131 (13) 4830-4838
31. Whitesides, G. M.; Grzybowski, B. Science 2002, 295 (5564) 2418-2421
32. Pasternack, R. F.; Gibbs, E. J.; Collings, P. J.; dePaula, J. C.; Turzo, L. C.; Terracina, A. J. Am. Chem. Soc. 1998, 120 (24) 5873-5878
33. Pasternack, R. F.; Bustamante, C.; Collings, P. J.; Giannetto, A.; Gibbs, E. J. J. Am. Chem. Soc. 1993, 115 (13) 5393-5399
34. Walba, D. M.; Korblova, E.; Shao, R.; Maclennan, J. E.; Link, D. R.; Glaser, M. A.; Clark, N. A. Science 2000, 288 (5474) 2181-2184
35. Wu, L.; Lal, J.; Simon, K. A.; Burton, E. A.; Luk, Y.-Y. J. Am. Chem. Soc. 2009, 131 (21) 7430-7443
36. Cox, J. S. G. Nature 1967, 216 (5122) 1328-1329
37. Cairns, H.; Fitzmaurice, C.; Hunter, D.; Johnson, P. B.; King, J.; Lee, T. B.; Lord, G. H.; Minshull, R.; Cox, J. S. G. J. Med. Chem. 1972, 15 (6) 583-589
38. Hartshorne, N. H.; Woodard, G. D. Mol. Cryst. Liq. Cryst. 1973, 23 (3/4) 343-368
39. Cox, J. S. G.; Woodard, G. D.; McCrone, W. C. J. Pharm. Sci. 1971, 60 (10) 1458-1465
40. Goldfarb, D.; Labes, M. M.; Luz, Z.; Poupko, R. Mol. Cryst. Liq. Cryst. 1982, 87 (3-4) 259-279
41. Lydon, J. E. Mol. Cryst. Liq. Cryst. 1980, 64 (1) 19-24
42. Hartshorne, N. H.; Woodard, G. D. Mol. Cryst. Liq. Cryst. 1981, 64 (5-6) 153-154
43. Attwood, T. K.; Lydon, J. E. Mol. Cryst. Liq. Cryst., Lett. Sect. 1986, 4 (1) 9-14
44. Kostko, A. F.; Cipriano, B. H.; Pinchuk, O. A.; Ziserman, L.; Anisimov, M. A.; Danino, D.; Raghavan, S. R. J. Phys. Chem. B 2005, 109 (41) 19126-19133
45. Lydon, J. Liq. Cryst. Today 2007, 16 (2) 13-27
46. Prasad, S. K.; Nair, G. G.; Hegde, G.; Jayalakshmi, V. J. Phys. Chem. B 2007, 111 (33) 9741-9746
47. Lauw, Y.; Leermakers, F. A. M.; Cohen Stuart, M. A. J. Phys. Chem. B 2007, 111 (28) 8158-8168
48. Castelletto, V.; Parras, P.; Hamley, I. W.; Baeverbaeck, P.; Pedersen, J. S.; Panine, P. Langmuir 2007, 23 (13) 6896-6902
49. Eguchi, K.; Kaneda, I.; Hiwatari, Y.; Masunaga, H.; Sakurai, K. J. Appl. Crystallogr. 2007, 40 (S1) s264-s268
50. Davies, T. S.; Ketner, A. M.; Raghavan, S. R. J. Am. Chem. Soc. 2006, 128 (20) 6669-6675
51. He, Y.; Li, Z.; Simone, P.; Lodge, T. P. J. Am. Chem. Soc. 2006, 128 (8) 2745-2750
52. Croce, V.; Cosgrove, T.; Dreiss, C. A.; Maitland, G.; Hughes, T.; Karlsson, G. Langmuir 2004, 20 (19) 7984-7990
53. Briseno, A. L.; Penkala, R. A.; Han, Y.-J.; Aizenberg, J.; Moon, H.; Lovinger, A. J.; Kloc, C.; Bao, Z. PMSE Prepr. 2004, 91, 890-891
54. Hiremath, R.; Basile, J. A.; Varney, S. W.; Swift, J. A. J. Am. Chem. Soc. 2005, 127 (51) 18321-18327
55. Han, T. Y.-J.; Aizenberg, J. Chem. Mater. 2008, 20 (3) 1064-1068
56. Dabros, M.; Thalladi, V. R. Chem. Commun. (Cambridge, U.K.) 2007, 24, 2476-2478
57. Cox, J. R.; Dabros, M.; Shaffer, J. A.; Thalladi, V. R. Angew. Chem., Int. Ed. 2007, 46 (12) 1988-1991
58. Cox, J. R.; Ferris, L. A.; Thalladi, V. R. Angew. Chem., Int. Ed. 2007, 46 (23) 4333-4336
59. Gupta, V. K.; Abbott, N. L. Langmuir 1996, 12 (10) 2587-2593
60. Tingey, M. L.; Wilyana, S.; Snodgrass, E. J.; Abbott, N. L. Langmuir 2004, 20 (16) 6818-6826
61. Gupta, V. K.; Abbott, N. L. Science 1997, 276 (5318) 1533-1536
62. Luk, Y.-Y.; Yang, K.-L.; Cadwell, K.; Abbott, N. L. Surf. Sci. 2004, 570 (1-2) 43-56
63. Van Nelson, J. A.; Kim, S.-R.; Abbott, N. L. Langmuir 2002, 18 (13) 5031-5035
64. Gupta, V. K.; Abbott, N. L. Phys. Rev. E: Stat. Phys., Plasmas, Fluids, Relat. Interdiscip. Top. 1996, 54 (5) R4540-R4543
65. Pale-Grosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113 (1) 12-20
66. Simon, K. A.; Burton, E. A.; Han, Y.; Li, J.; Huang, A.; Luk, Y.-Y. J. Am. Chem. Soc. 2007, 129 (16) 4892-4893
67. Hartshorne, N. H.; Stuart, A., Crystals and the Polarizing Microscope, 4 th ed.; American Elsevier Pub. Co.: New York, 1970; p 614 ff.
68. Nastishin, Y. A.; Liu, H.; Schneider, T.; Nazarenko, V.; Vasyuta, R.; Shiyanovskii, S. V.; Lavrentovich, O. D. Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys. 2005, 72 (4-1) 041711/1-041711/14
69. Park, H.-S.; Kang, S.-W.; Tortora, L.; Nastishin, Y.; Finotello, D.; Kumar, S.; Lavrentovich, O. D. J. Phys. Chem. B 2008, 112 (51) 16307-16319
70. Edwards, D. J.; Jones, J. W.; Lozman, O.; Ormerod, A. P.; Sintyureva, M.; Tiddy, G. J. T. J. Phys. Chem. B 2008, 112 (46) 14628-14636
71. Tomasik, M. R.; Collings, P. J. J. Phys. Chem. B 2008, 112 (32) 9883-9889
72. Horowitz, V. R.; Janowitz, L. A.; Modic, A. L.; Heiney, P. A.; Collings, P. J. Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys. 2005, 72 (4-1) 041710/1-041710/10
73. Ruslim, C.; Matsunaga, D.; Hashimoto, M.; Tamaki, T.; Ichimura, K. Langmuir 2003, 19 (9) 3686-3691
74. Bonazzi, S.; De Morais, M. M.; Garbesi, A.; Gottarelli, G.; Mariani, P.; Spada, G. P. Liq. Cryst. 1991, 10 (4) 495-506
75. Tao, F.; Bernasek, S. L. Chem. Rev. 2007, 107 (5) 1408-1453
76. Luk, Y.-Y.; Tingey, M. L.; Hall, D. J.; Israel, B. A.; Murphy, C. J.; Bertics, P. J.; Abbott, N. L. Langmuir 2003, 19 (5) 1671-1680
77. Boese, R.; Weiss, H.-C.; Blaser, D. Angew. Chem., Int. Ed. 1999, 38 (7) 988-992
78. Bond, A. D. New J. Chem. 2004, 28 (1) 104-114
79. Chidsey, C. E. D.; Loiacono, D. N. Langmuir 1990, 6 (3) 682-691
80. Nuzzo, R. G.; Dubois, L. H.; Allara, D. L. J. Am. Chem. Soc. 1990, 112 (2) 558-569
81. Barbero, G.; Durand, G. J. Appl. Phys. 1990, 67 (5) 2678-2680
82. Miller, W. J.; Abbott, N. L.; Paul, J. D.; Prentiss, M. G. Appl. Phys. Lett. 1996, 69 (13) 1852-1854
83. Collings, P. J. Liquid Crystals: Natures Delicate Phase of Matter, 2 nd ed.; Princeton University Press: Princeton, 2002; p 200 ff.
84. Lavrentovich, M.; Sergan, T.; Kelly, J. Liq. Cryst. 2003, 30 (7) 851-859
85. Fujiwara, T.; Ichimura, K. J. Mater. Chem. 2002, 12 (12) 3387-3391
86. Hui, Y. W.; Kuzma, M. R.; San Miguel, M.; Labes, M. M. J. Chem. Phys. 1985, 83 (1) 288-292
87. Helfinstine, S. L.; Lavrentovich, O. D.; Woolverton, C. J. Lett. Appl. Microbiol. 2006, 43 (1) 27-32
88. Lydon, J. Curr. Opin. Colloid Interface Sci. 2004, 8 (6) 480-490
89. Private communication with Nicholas Abbott.
90. Dierking, I.; Lagerwall, S. T. Liq. Cryst. 1999, 26 (1) 83-95
91. Kitzerow, H.-S. Chirality Liq. Cryst. 2001, 296-354
92. Drzaic, P. S. J. Appl. Phys. 1986, 60 (6) 2142-2148
93. Doane, J. W.; Vaz, N. A.; Wu, B. G.; Zumer, S. Appl. Phys. Lett. 1986, 48 (4) 269-271
94. Tortora, L.; Park, H. S.; Antion, K.; Finotello, D.; Lavrentovich, O. D. Proc. SPIE-Int. Soc. Opt. Eng. 2007, 6487, 64870I/1-64870I/15
95. Lockwood, N. A.; Gupta, J. K.; Abbott, N. L. Surf. Sci. Rep. 2008, 63 (6) 255-293
96. Jang, C.-H.; Tingey, M. L.; Korpi, N. L.; Wiepz, G. J.; Schiller, J. H.; Bertics, P. J.; Abbott, N. L. J. Am. Chem. Soc. 2005, 127 (25) 8912-8913
97. Bajc, J.; Bezic, J.; Zumer, S. Phys. Rev. E: Stat. Phys., Plasmas, Fluids, Relat. Interdiscip. Top. 1995, 51 (3-A) 2176-2189
98. Luckhurst, G. R. Thin Solid Films 2006, 509 (1-2) 36-48
99. Cheng, L.-L.; Luk, Y.-Y.; Murphy, C. J.; Israel, B. A.; Abbott, N. L. Biomaterials 2005, 26 (34) 7173-7182
100. Luk, Y.-Y.; Jang, C.-H.; Cheng, L.-L.; Israel, B. A.; Abbott, N. L. Chem. Mater. 2005, 17 (19) 4774-4782
101. Ruiz, R.; Kang, H.; Detcheverry, F. A.; Dobisz, E.; Kercher, D. S.; Albrecht, T. R.; de Pablo, J. J.; Nealey, P. F. Science 2008, 321 (5891) 936-939
102. Gin, D. L.; Pecinovsky, C. S.; Bara, J. E.; Kerr, R. L. Struct. Bonding (Berlin, Ger.) 2008, 128, 181-222
103. Liu, S.; OBrien, D. F. J. Am. Chem. Soc. 2002, 124 (21) 6037-6042
104. Tam-Chang, S.-W.; Helbley, J.; Carson, T. D.; Seo, W.; Iverson, I. K. Chem. Commun. 2006, 5, 503-505